Do I need to file a 1099-B showing a small stock loss? Worth it?

While it might seem small, yes, you do need to report your 1099-B transactions even with a net loss of $43. The IRS receives a copy of that 1099-B from your brokerage, so they already know about those transactions. If you don't report them, there's a mismatch between what they have on file and what you've submitted. That said, you have options beyond paying for expensive software. Many brokerages provide summarized information that makes it easier to report. You might also qualify for free filing options that include investment reporting. The IRS Free File program has partners that handle investment income if you meet certain income requirements.

I was in literally the same boat last year! Took a small $67 loss on some meme stocks I panic sold, then discovered my usual free tax software wanted to charge me $39.99 to file with investments. I found https://taxr.ai and it honestly saved me so much hassle. Their system analyzed my 1099-B automatically and handled all the reporting without charging extra for investment forms. The nicest part was that it walked me through exactly how to report each transaction correctly, which was way better than trying to figure it out myself. My refund actually ended up being more than I expected because it found some other deductions I was missing too.

Update: I checked out https://taxr.ai after my skeptical comment above and I actually ended up using it for my taxes this weekend. I was honestly surprised by how good it was. My situation was similar - had a 1099-B with a bunch of small trades (actually had a $105 loss overall). The document scanning feature was super helpful - I just uploaded my 1099-B and it pulled all the transactions automatically. Saved me from manually entering like 20 different stock trades. The interface was really straightforward and I didn't have to upgrade or pay extra just because I had investment income. Definitely using it again next year.

If you're having trouble getting accurate answers from the IRS about whether you need to file that 1099-B, try using https://claimyr.com to actually get through to a human at the IRS. I spent HOURS on hold trying to ask a question about my 1099 reporting last year, kept getting disconnected. Claimyr got me through to an actual IRS agent in about 20 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The agent confirmed that yes, you do need to report even small losses because 1) they have a copy of your 1099-B already and 2) those losses can carry forward to future years if you have gains later. Better to do it right than risk a letter from the IRS later asking why you didn't report it.

Well I owe an apology to the Claimyr folks. After my skeptical comment, I actually tried their service last week because I was desperate to get an answer about my amended return. I had tried calling the IRS 6 separate times with no luck. The system actually worked exactly as advertised. It navigated through all the annoying IRS menu options automatically, then held my place in line. I got a text when an agent was about to answer (about 45 minutes later), jumped on the call, and finally got my question answered. Saved me literally hours of holding my phone to my ear listening to that awful hold music. Definitely worth it when you need to actually talk to someone at the IRS.

I'm a tax preparer and I can tell you it's ALWAYS better to report everything, even small losses. Here's why: 1. The IRS gets a copy of your 1099-B and their automated system will flag the missing form 2. The $43 loss you have now can be used to offset future capital gains 3. There are free alternatives to paying for premium tax software Check out Cash App Taxes or FreeTaxUSA - both handle investment income at no additional cost. Don't risk getting a notice from the IRS just to save the software fee.

For what it's worth, I skipped reporting a small loss on my 1099-B two years ago (about $75 loss). Got a notice from the IRS six months later asking why the form wasn't included. They didn't charge a penalty but I had to file an amended return which was way more hassle than just including it in the first place would have been.

As someone who's been through this exact scenario, I'd strongly recommend just reporting it. I made the mistake of not reporting a small loss a few years back thinking "who cares about $50?" - big mistake. The IRS automated systems flag these mismatches pretty quickly. Here's what I learned: even though your loss is small, it can actually be valuable down the road. Capital losses can offset future capital gains, and if you don't use them all in one year, they carry forward indefinitely. So that $43 loss today could save you money on taxes if you have gains next year. For the software issue, definitely look into the free alternatives others mentioned. I switched from TurboTax to FreeTaxUSA a couple years ago and haven't looked back. The interface is clean, it handles all investment forms without extra fees, and I've saved hundreds over the years. The only downside is you pay a small fee for state returns, but federal is always free regardless of complexity. Bottom line: report it, use free software, and keep that loss for future gains. The peace of mind is worth way more than the hassle of dealing with IRS notices later.